You May Hate Planning, But You Should Do It Anyway

Some of the smartest people that I have ever met struggle with convincing themselves to do one thing: plan their work.

They’re off the charts in terms of analyzing all sorts of things from manufacturing processes to stocks to nuclear particles. But when it comes to their own time management or laying out a plan to get a big project done, they balk. Something about scheduling makes their brains shut down, and they can go from brilliant to blank in an instant.

One of the reasons these individuals struggle is because they can get away with not planning for much longer than most. If you have some charisma and a strong ability to cram, you may have been able to pull off decent work at the last minute — or at least find ways to get an extension. If you can continue in this way without any major issues, there’s no need to change.

But as time demands increase — you get a new job, you’re short staffed, you get married or have kids, or your health changes — a life without planning or routines can make you tired at best, and miserable at worst. At some point, you need to decide that it’s worth the time and effort to create plans and routines. Based on my experience with time management clients, here are some tough truths about planning that every individual needs to accept before moving forward. Once you accept them and make planning a habit, you can harness its power to create a happier, healthier, and more productive life.

Planning will trigger pain — at least initially. If you have very weak planning patterns in your brain, you will literally feel pain when you begin to plan. It’s like when you start a new exercise routine and work out muscles that you didn’t even know that you had. But as you develop the habit of planning, the pain associated with it usually decreases. And the more positive reinforcement you get only increases, the more you do it.

For example, Camille Fournier, former CTO of Rent the Runway, described the pain and reward of planning. She faced stress and frustration when she first began planning her projects, explaining how her boss would dissect her plans — anywhere that had uncertainty or risk — and ask her to go back and reconsider it. “It was absolutely dreadful,” she said, “and I found myself deeply frustrated and impatient throughout the process. And yet, at the end of it all, we broke this big project down into deliverable chunks, and I went on to successfully lead a significant architectural change that ran close to on schedule, despite its complexity. The memory of the frustration of planning is burned into my brain, but so is the memory of the huge accomplishment that came out of that planning.”

In some cases, planning works best when you don’t have to go it alone. Consider planning out a major project as a team or at least with one other person. Depending on the size of the team and the overlap of the work, it can also make the process easier to break down monthly goals into a weekly plan together.

Planning takes longer than expected (and so does the work). It’s typical for planning your week to take 30-60 minutes and project planning to take much longer. For those unfamiliar with planning, this can seem like an excessive amount of time. But for those who have seen its power, they understand that one hour a week can make hundreds of hours of thoughtful work less stressful and more productive.

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What’s more, part of the benefit of planning is that you gain greater clarity on how long work actually takes versus how long you thought it would take. This can lead to some more frustration initially because you have to face the fact that the reality is different than what you hoped. Planning also doesn’t mean that everything will go according to schedule. But it does allow you to know early on if something goes off-course, so you can do something about it, rather than getting stuck with little to no options later.

Things tend to go better when you plan. When you plan, you’ll often discover some hard truths about what it will take to accomplish a project or simply get your work done this week. This can feel a bit uncomfortable because you’re no longer in a happy imaginary world where there’s an infinite amount of time, you can get everything done all at once, and make everyone happy. But discovering these facts as early as possible gives you the ability to quickly negotiate expectations on deliverables or pull in more resources on a project. It’s also helps you to confidently set boundaries and decide what you’re going to do for the day because you’re aware of your full array of options and the current priorities. This maximizes your effectiveness and allows you to consistently set and meet expectations.

Planning becomes the canary. In the past, miners brought canaries into mines as an early detection warning system. If the canaries died, it was a sign that the toxic gases were rising and the miners needed to get out. Planning can provide the same sort of early warning signals — if you veer significantly off of your estimated plan, it’s a sign that something is wrong and adjustments need to be made. Having a plan and checking against it allows you to notice and make those adjustments before your projects or other time commitments are in major peril.

Many individuals who don’t like to plan tend to abandon planning quickly, assuming that they have things under control. But that sends them in a downward spiral. Keeping an eye on the plan and making adjustments is just as important as delivering a complete product — it maintains process stability. If you ignore the canary, you have a greater chance of failing, just because you didn’t notice important signs.

Can planning be difficult? Yes. But is it possible for you to do more of it? Absolutely. The payoff of going through the pain of planning can be huge in terms of increased productivity, decreased stress, and most of all intentional alignment with what’s most important.